Domino synthesis of 5-aminoimidazoles from Strecker multicomponent adducts via ytterbium-promoted isocyanide insertion/5-exo-dig cyclization
| Autor: | Rolando Cannalire, Camilla Russo, Paolo Luciano, Bruno Cerra, Antimo Gioiello, Francesca Brunelli, Gian Cesare Tron, Mariateresa Giustiniano |
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| Přispěvatelé: | Cannalire, Rolando, Russo, Camilla, Luciano, Paolo, Cerra, Bruno, Gioiello, Antimo, Brunelli, Francesca, Tron, Gian Cesare, Giustiniano, Mariateresa |
| Rok vydání: | 2022 |
| Předmět: |
Organic Chemistry
Domino reaction Isocyanides General Medicine Catalysis 5-Aminoimidazole Inorganic Chemistry Lewis acid catalysis Isocyanide Multicomponent reactions Drug Discovery Lewis acid catalysi Isocyanides Domino reactions Multicomponent reactions Lewis acid catalysis 5-Aminoimidazoles Domino reactions Physical and Theoretical Chemistry 5-Aminoimidazoles Molecular Biology Information Systems |
| Zdroj: | Molecular Diversity. 27:511-515 |
| ISSN: | 1573-501X 1381-1991 |
| DOI: | 10.1007/s11030-022-10418-4 |
| Popis: | A new Lewis acid promoted domino isocyanide insertion/5-exo-dig cyclization of readily available Strecker 3-component adducts to 4-substituted 5-aminoimidazole derivatives is herein reported. Despite their potential as relevant heterocyclic scaffolds in medicinal chemistry programs, this class of compounds is still underrepresented, with current synthetic strategies poorly efficient in terms of timing and yields. To this end, we show how the exploitation of unconventional reactivities of isocyanides, promoted by ytterbium-triflate, could represent a key resource to enable a fast and easy access to such an unexplored area of the chemical space. |
| Databáze: | OpenAIRE |
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